HCID 10542715, compound → HCID 10660122, compound

HRID 2245198Notes

Reaction equation

HRID 2245198 reaction equation
[CH2:1]([N:7]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]>C(OCC)(=O)C.[Pd]>[CH2:17]([N:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 1

HCID 10542715HCID 10542715, compound

Product 1

HCID 10660122HCID 10660122, compoundYield 102.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 25.0 grams of N,N-di-n-hexyl-N-(4-nitrophenyl)amine in 100 ml of ethyl acetate containing 3.02 grams of 10% palladium on activated charcoal was hydrogenated at 40 psi for 1.5 hours. The solution was filtered and concentrated in vacuo to yield 23.2 grams of product as a colorless oil. 1H NMR (CDCl3) δ 6.4(AB quartet, 4H), 3.3(bs, 2H), 3.15(t, 4H), 1.5(pent, 4H), 1.2-1.4(m, 12H), 0.9(t, 6H).

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6be3ecde3c864b64a2f4695d3fca2ee9
Source dataset
uspto-grants-2010_03
Patent number
US07683017B2

Reaction notes

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